Book Windham County Hotels

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Cities in Windham County

HotelsHotels

Brattleboro

Brattleboro

Filter by

Popular filters
Popular filters
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top Hotels in Windham County

The Covered Bridge Inn
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, 1,008 reviews
"Fireplace was very nice. Room was adequate."
The price is AU$124
per night
13 June - 14 June
The Covered Bridge Inn
Mount Snow Grand Summit Resort
Exterior
Mount Snow Grand Summit Resort
3.0 star property
8.8 out of 10, Excellent, 119 reviews
"This was such a great find! First time staying at a ski resort and it was perfect! Really enjoyed the ski in / ski out. We had beautiful views from our room complete with balcony overlooking the slopes! Loved the heated outdoor pool and hot tubs. Fire pits outside were also nice to have. Very cozy atmosphere. Everyone was very friendly and helpful at the hotel."
The price is AU$245
per night
12 June - 13 June
Mount Snow Grand Summit Resort
Colonial Motel And Spa
Exterior
Colonial Motel And Spa
3.0 star property
7.0 out of 10, Good, 1,001 reviews
"Very comfortable and relaxed "
The price is AU$146
per night
9 June - 10 June
Colonial Motel And Spa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
The Black Bear Lodge at Stratton Mountain Resort
10 restaurants, lunch, dinner served; American cuisine
The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
7.4 out of 10, Good, 830 reviews
"This is the third time we have stayed at the black bear lodge in Stratton and every time we stay our experience is the same.. excellent. The staff are all so nice and accommodating, the property is clean and the breakfast is perfect. The rooms are comfortable and clean, it really is the perfect place to stay in Vermont. See you in October. "
The price is AU$264
per night
9 June - 10 June
The Black Bear Lodge at Stratton Mountain Resort
Mountaineer Inn
Fireplace
Mountaineer Inn
2.0 star property
9.2 out of 10, Wonderful, 291 reviews
"Loved that this is a legit old ski lodge and still has the feel while having modernized what needed to be. Loved it here."
The price is AU$213
per night
10 June - 11 June
Mountaineer Inn
The Four Chimneys Inn
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10
The Four Chimneys Inn
4.0 star property
9.4 out of 10, Exceptional, 257 reviews
"We quite liked this hotel as it was charming and well thought out in many ways. We especially loved the dinner we had the first night. Our room had a fireplace and we loved that feature because it was a bit chillier than we expected. The only thing we would have wished for was a mini fridge in the room, but that’s not a huge deal breaker for us to return someday. It Is a nice walkable area and an easy to navigate town. Sadly, Bennington Pottery store isn’t open to the public anymore, but the...
The price is AU$417
per night
12 June - 13 June
The Four Chimneys Inn
The Upper Pass Lodge at Magic Mountain
Restaurant
The Upper Pass Lodge at Magic Mountain
2.5 star property
8.4 out of 10, Very good, 558 reviews
"Clean hotel, pet friendly. "
The price is AU$148
per night
9 June - 10 June
The Upper Pass Lodge at Magic Mountain
Paradise Inn
Seasonal outdoor pool, pool umbrellas, pool loungers
Paradise Inn
2.5 star property
8.2 out of 10, Very good, 1,001 reviews
"We were late coming in and the owner was accommodating! It was quiet and clean -- not new and modern, but great for the price!"
The price is AU$294
per night
23 June - 24 June
Paradise Inn
Hampton Inn Brattleboro
Lobby
Hampton Inn Brattleboro
2.5 star property
8.4 out of 10, Very good, 904 reviews
"Very helpful at check-in "
The price is AU$229
per night
3 July - 4 July
Hampton Inn Brattleboro
Blue Vista Motor Lodge
Outdoor spa tub
Blue Vista Motor Lodge
2.0 star property
9.8 out of 10, Exceptional, 115 reviews
"Blue Vistais a gem. We loved everything about it especially the staff."
The price is AU$282
per night
10 June - 11 June
Blue Vista Motor Lodge
Travelodge by Wyndham Brattleboro VT
Reception
Travelodge by Wyndham Brattleboro VT
2.5 star property
6.0 out of 10, 627 reviews
"The property is clean and well maintained "
The price is AU$140
per night
1 July - 2 July
Travelodge by Wyndham Brattleboro VT
The Putney Inn
Exterior
The Putney Inn
2.5 star property
8.2 out of 10, Very good, 910 reviews
"Though there were some simple things that needed attention in the room, it was overall clean and presentable. I would certainly stay there again."
The price is AU$198
per night
9 June - 10 June
The Putney Inn
Sun Lodge
Sundeck
Sun Lodge
3.5 star property
8.6 out of 10, Excellent, 260 reviews
"Stayed overnight when traveling for business, lovely lodge with friendly staff and I was able to get a good nights rest. Comfortable and clean, highly recommend!"
Sun Lodge
The White House Inn
Balcony view
The White House Inn
3.5 star property
9.2 out of 10, Wonderful, 179 reviews
"Very pleasantly surprised. The staff was very friendly and helpful. They accommodated all of our needs."
The price is AU$455
per night
20 June - 21 June
The White House Inn
Black Mountain Inn
Front of property
Black Mountain Inn
2.0 star property
7.2 out of 10, Good, 378 reviews
"Good stay. Good price. Clean and comfortable. Friendly staff. Walk to restaurants. "
The price is AU$189
per night
12 June - 13 June
Black Mountain Inn
Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel
Exterior
Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, 894 reviews
"Really clean, peaceful spot, with easy parking, friendly staff, and overall good atmosphere."
The price is AU$330
per night
9 June - 10 June
Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel
The Autumn Inn
Front of property
The Autumn Inn
2.0 star property
7.8 out of 10, Good, 503 reviews
"Independent motel, somewhat dated but clean with updated bathroom. Gentleman who assisted me was lovely. Short visit to Bennington to visit an elderly family member. Convenient, although I wish I could find better coffee close by. I launched early morning on low grade."
The price is AU$146
per night
6 June - 7 June
The Autumn Inn
Best Western Springfield Hotel
Lobby
Best Western Springfield Hotel
2.5 star property
8.8 out of 10, Excellent, 684 reviews
"Food options fairly close, fuel options very close, the room was clean but had a hole in the carpet which was very evident. "
The price is AU$294
per night
16 June - 17 June
Best Western Springfield Hotel
Big Bears Lodge
Outdoor spa tub
Big Bears Lodge
3.0 star property
8.8 out of 10, Excellent, 149 reviews
"Staff very accommodating! Loved the place."
The price is AU$265
per night
13 June - 14 June
Big Bears Lodge
Hampton Inn Bennington
Exterior
Hampton Inn Bennington
2.5 star property
8.6 out of 10, Excellent, 876 reviews
"Wish there were bigger towels in pool area. And sauna needs re-do. Staff is great, breakfast and coffee station is great. "
The price is AU$263
per night
16 June - 17 June
Hampton Inn Bennington
Don't see what you're looking for?
See all available properties in Windham County
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Windham County Travel Info

Best cities to visit
Stratton, Londonderry and Wilmington
Hotels with skiing
1,274
Number of hotels
585
Lowest price
AU$124
Highest price
AU$455
Top attractions
Magic Mountain Ski Resort, Viking Nordic Centre and The Ledge

Frequently asked questions

How much do hotels in Windham County cost?
The season and factors like Christmas, Easter and school holidays can affect the price of a hotel in Windham County. You can find cheap options from AU$124 in a few different ways on Expedia. First, enter the dates you’d like to get away, then use the filters like amenities and property type to narrow your search. You can also sort by price, so the most affordable options appear at the top.
When is the best time to go to Windham County?
Here are some facts that might help you decide when to travel: Windham County has a humid continental climate. The summer months are between June and August. If you prefer to go during this season, you can expect average temperatures to range from 12ºC to 24ºC. The best time to plan a visit to Windham County depends on what you want to get out of your holiday.
How can I find cheap hotels in Windham County?
Windham County cheap hotels start at AU$124 per night. To find these types of wallet-friendly options, make use of our “Price per night” filter. Like some other tips? Be flexible with your dates and book ahead of time. Browse our cheap hotels in Windham County page for bargains that are hard to resist.
What are the best hotels in Windham County for families?
Pack your bags (and the kids!) and get ready for an action-packed getaway at one of our top family-friendly properties in Windham County. Located in South Londonderry, Charming And Private Farm House is an excellent pick. A playground and a nearby beach are two of the amenities here. Or chill out with the fam at Three Mountain Inn. You can also find your ideal stay by clicking on the “Family friendly” box in the “Traveller experience” section of our handy filters.
Why should I book my Windham County hotel with Expedia?
Amazing prices on Windham County hotels are just the start of the reasons to book with Expedia. Become an Expedia Rewards member for free today and earn points on every eligible booking, along with fantastic membership perks. We’re talking instant savings of 10% or more on over 100,000 hotels worldwide! Plus, most of our hotels feature free cancellation, so you can lock in the escape of your dreams without having to worry about your plans changing.

Recent Reviews in Windham County
Expedia verified reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

5/5 Excellent
"This is the third time we have stayed at the black bear lodge in Stratton and every time we stay our experience is the same.. excellent. The staff are all so nice and accommodating, the property is clean and the breakfast is perfect. The rooms are comfortable and clean, it really is the perfect place to stay in Vermont. See you in October. "
A verified traveller stayed at The Black Bear Lodge at Stratton Mountain Resort
Posted 9 days ago
The Black Bear Lodge at Stratton Mountain Resort
The Putney Inn

The Putney Inn

5/5 Excellent
"Easy, quick check in, friendly staff. Some noise from neighbors to be expected. Very clean, good sleep, pleasant stay. Would return. "
A verified traveller stayed at The Putney Inn
Posted 2 weeks ago
The Putney Inn